


The Destiel Drama Club

by vedaine



Category: Supernatural
Genre: Alternate Universe - High School, Anal Fingering, Bisexual Dean Winchester, Crossdressing Castiel, Frottage, Gay Castiel (Supernatural), M/M, Oral Sex, Romeo and Juliet References, Theater Nerd Castiel (Supernatural), Virgin Castiel, Virgin Dean Winchester
Language: English
Status: Completed
Published: 2018-08-27
Updated: 2018-08-27
Packaged: 2019-07-03 08:38:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,680
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15815355
Author URL: https://archiveofourown.org/users/vedaine/pseuds/vedaine
Summary: Dean sees a gorgeous girl signing up for the fall play auditions and he decides to try out as well. But when Dean takes his co-star Castiel out on a date, he realizes that "she" isn't quite what he was expecting.





	The Destiel Drama Club

He had promised Sam he’d try. Didn’t mean he had to like it. Dean pushed open the door and approached his certain doom.

The Verona Area High School extracurricular clubs and organizations open house took up the full gymnasium. Teenagers were running between tables, excited shouts filled the air as students met up with friends they hadn’t seen all summer, and Dean was miserable.

He was entering his senior year at his fourth high school in as many years, and he promised Sam he’d try to be social, try to make friends. And Sam had insisted that he do so by joining an extracurricular club.

Much to Dean’s chagrin, they’d moved to town only a day ago—their high school enrollment paperwork was still being processed—and he’d missed the cut off for the wrestling team tryouts. So now he was stuck here, surrounded by teenagers who were happy, who had their whole lives to look forward to, and who had no clue about the things that go bump in the night. Whereas Dean knew all too well the monsters out there; he’d helped his dad on smaller hunts before. The only reason Dean was even still in high school was to set a good example for Sam, and to keep the both of them off the radar of social services.

At least the chicks were fairly cute here, he thought, as a blonde cheerleader passed him. She checked him out, and he winked at her.

Then he saw the girl. He couldn’t decide if she was cute or gorgeous, but either way, he was smitten. Olive skin, inky black hair in a pixie cut pulled back with a headband, and a lemon yellow sundress covered in bees. She was fairly flat chested but her arms and legs were beautifully toned—probably a runner. Dean felt instantly drawn to her.

She was chatting with another girl who was staffing one of the tables, and then she scribbled something on the clipboard on the table. Dean sidled up behind her, hoping to at least learn her name.

He was startled when she abruptly turned around, knocking their foreheads together.

“I’m so sorry. Are you okay?” the girl stammered, her voice rich and husky.

Dean stared. She had the most beautiful sky-blue eyes he’d ever seen. He could get lost in those eyes, he could see oceans in those eyes. Dean realized he was still staring, and that she was waiting for him to say something.

“Yeah, peachy,” he said, smiling. Peachy? Where the heck had that come from?

“Good. See you around, handsome.” She gave him a gummy smile and swished away, throwing him a wink over her shoulder.

That was definitely a girl he could fall for. Then Dean realized that he’d forgotten to get her name. He looked over at the table she’d been at—the Verona High Drama Club. On the table was a clipboard reading, “Sign up for the fall play auditions.” The most recent entry on the signup sheet was Castiel Novak. Castiel was her name, and she was perfect. Dean grabbed the pen and added his name right below hers.

As Dean had expected, the next day Sam forced him to follow through with drama club, even going so far as to help him practice a monologue for the audition. Dean had seen his dream girl—Castiel—briefly at the audition, but he’d been too nervous about having to speak on the stage to even considering approaching her.

One week later, on the second full day of school, the cast list went up on the bulletin board in the cafeteria. Dean couldn’t pull his eyes away from the sheet of paper. Dean Winchester—Romeo. He’d gotten the lead. But then he saw something that made his heart flutter: Castiel Novak—Juliet.

His dream girl, acting across from him. He was pretty sure Romeo and Juliet even had a kissing scene. They’d need to practice that for sure. Maybe even “run lines” some weekend if he was lucky.

The first day of after-school rehearsals, Dean finally introduced himself to Castiel. She was also a senior, also 18, and was a long-time member of drama club. Castiel wasn’t just pretty, she was funny, and smart, and Dean was falling for her already.

The 7th day of after-school rehearsals, on a Thursday, Dean asked her out. She said yes.

* * *

At Sam’s suggestion, Dean planned a picnic in the park, where there was also a small jazz festival going on. Sam had been reading a women’s magazine about first dates, and it had stressed that it be somewhere well-lit, public, and that they could arrive at separately. Dean was a little pissed off that such things were necessary, but knew he would do just about anything to make sure that Castiel was comfortable.

They met at the park, Dean in jeans and Cas in a blue sundress, and found a nice patch of grass to set down the picnic blanket.

“This is amazing, thank you Dean. How did you decide on a picnic?”

“It was Sammy’s idea—Sammy’s my brother, by the way. I told him I had a date with the prettiest girl in school, and he said I ought to do it right. He’s only 13, but he’s real smart. Gonna go to Stanford, he says, and become a lawyer. I don’t doubt it.” Dean smiled at Castiel, pride for his brother showing through.

Castiel’s stomach had dropped. “Dean, I’d assumed you’d realized. It’s common knowledge around school, and I forgot you’re new here, and oh god please don’t hate me…”

“Cas? What’s wrong?”

“I’m not a girl,” Castiel mumbled, tripping over his words. “I just wear dresses. I like to look pretty. I’m gay, and I’m a boy. Oh god I’m so sorry, please don’t hate me. Please don't hurt me.” A fat teardrop streaked down his cheek as he stood up to leave.

“Hey, sit down. I don’t hate you, and I would never hurt you,” Dean said, wiping the tear from Castiel’s face. “It’s my fault for assuming. Doesn’t mean we need to cancel our date.”

“What?”

“You’re smart, and funny, and ridiculously pretty. Doesn’t make a difference to me whether you’re a dude or a chick. Not like I’m on the straight-and-narrow or anything like that.” Dean winked.

“What?” Castiel repeated himself.

“Let me break it down for you. I’m bi, and I’m into you, and I’d still like to date you, Cas.”

“Oh.” Cas looked at Dean, puzzled but beginning to smile. “You called me Cas.”

“Yeah, sorry, I tend to give people I like nicknames.”

“It’s okay, I like it.”

“Good.”

They talked for hours, about everything and nothing.

Dean talked about his family, absentee father and dead mother, and how he was essentially raising Sam on his own. About the pressure Dean felt to go into the family business, and how what he really wanted to do was be a mechanic. About his love for classic cars, classic rock, and Dr. Sexy.

Castiel talked about his family, religious to a fault, who’d kicked him out for being gay and for wearing dresses. About the cousin Gabriel who he now lived with, who accepted him fully for who he was. About his dream of professional acting, his fear that he wouldn’t be accepted in the theater world as a guy playing women’s parts, and his plan to major in theater arts at Kansas State next year. About his love of bees, burgers, and Netflix.

When one of the live bands started a set, Dean stood up and offered his hand to Castiel, dragging him over to the makeshift dance floor in front of the stage. They swayed back and forth to the jazz trio.

“You know, Cas, we’re going to have to kiss in the play.”

Castiel felt his throat go dry and licked his chapped lips, glancing down at Dean’s mouth. “Yes,” he whispered.

“We should probably practice.”

“Yes,” Castiel whispered again.

Dean brought one hand up to Castiel’s cheek, feeling the start of a five-o’clock shadow, and leaned forwards. Capturing Castiel’s lips in a chaste kiss, he then leaned his forehead against Castiel’s.

“Was that alright?” Dean shyly asked, a pink blush covering his freckles.

Castiel looked Dean in the eyes and smiled. Throwing his arms around Dean’s neck, he brought their pelvises against one another and slammed their mouths back together. Grinding to the music, getting hard against the other’s thighs, they made out passionately, all teeth and tongues and panting and moaning.

As the band finished its final song, and the scattered audience began to applaud, Dean and Castiel suddenly remembered that they were still on the dance floor. It was now night, and dark.

“Walk me to my car?” Castiel asked breathlessly.

“Yes,” Dean whispered.

“Try and walk somewhat in front of me. It’s really hard to hide a boner in a dress.”

Dean grabbed Castiel’s hand, scooping up their picnic supplies and racing him into the parking lot. “Where’s your car?”

“Far side of the lot. Where’s yours?”

“Closer. C’mon.” Dean pulled Castiel towards the ‘67 Chevy Impala and unlocked the doors, scrambling into the backseat with Castiel close behind him.

Shutting the door, Castiel straddled Dean, who was reclining at an angle on the bench seat. Glad of the darkness and poorly lit parking lot, Dean tilted his head up to capture Castiel’s mouth with his. Despite Castiel’s lips looking chapped, they were covered in a thin layer of cherry chapstick, and Dean greedily sucked on the boy’s lower lip.

“You taste so good, Cas,” Dean mumbled against Castiel’s mouth.

“Less talking, more touching.”

Castiel grabbed Dean’s hands, which had been looped around his lower back, tugged Dean’s henley off, and moved Dean’s hands to the top of his thighs. Dean’s hands were now touching above Castiel’s knees, fingers dancing just below the hem of his dress. Dean looked up at Castiel, wondering just how far the other boy would be willing to go tonight, when Castiel sharply ground their pelvises together.

“Anything short of full sex is on the table,” Castiel moaned into Dean’s ear, understanding the other boy’s hesitation. “Not going to give you my v-card—tonight, at least—but you’d damn well better get me off.”

Dean moaned and moved his hands up Castiel’s dress. Reaching his hips, Dean unintentionally bucked up when he made the discovery—Castiel was wearing panties. Lace, by the feel of them.

“God damn, Cas. You trying to kill me?”

“You like them, Dean?”

“You’re incredible,” Dean said.

Dean began to suck at Castiel’s neck as he slid his hands backwards to squeeze the boy’s ass through his panties. Their pelvises were still grinding together in a decreasingly gentle rhythm, both teens rock hard, smearing precum inside their respective underwear. With a bite to Castiel’s clavicle, Dean slid the back of the panties down slightly, uncovering Castiel’s pert ass. Dean circled a dry finger around Castiel’s asshole, feeling the pucker catch on the rough pad of his finger.

“God, yes, Dean. Please. Touch me,” Castiel whined.

“Open your mouth,” Dean said, bringing the hand to Castiel’s lips and sticking two fingers in. Castiel kept eye contact with Dean, sucking and tonguing the fingers as Dean gasped at the sight. He withdrew his finger, thin threads of spit still connecting them to Castiel’s lips, and returned the hand to Castiel’s ass.

At this point, they weren’t even kissing anymore, their foreheads tight together, mouths nearly touching as they panted heavily.

Dean circled Castiel’s asshole with one finger, and slowly breached his hole up to the first knuckle. Castiel froze for a moment before resuming humping Dean’s lap.

“More. Dean, more.”

“Hang on.”

Gently removing his finger from Castiel’s hole, Dean shuffled the other teen enough to fully pull his panties off. Dean then swiftly undid his own jeans and pulled them, and his boxers, down around his ankles.

Lining up their cocks, both boys moaned at the feel of them finally moving together, slickened by both of their precum. Dean was circumcised, his thick cock’s head glistening purple. Castiel's cock was thinner but longer, and his foreskin was pulled back, exposing his weeping slit.

Dean returned his finger to Castiel’s hole and slowly pushed it in, breaching both rings of muscle. The boy was so tight, Dean didn’t think he’d be able to fit another finger in. Dean crooked his finger, searching for Castiel’s prostate before locating the sensitive glad and gently rubbing it.

“God, yes, Dean,” Castiel cried, grabbing both their cocks in his hand and beginning to jack them off together. “Keep going, please.”

“Fuck, Cas,” Dean said. “I’m so close already.”

“Me too.”

Castiel came first, the dual stimulation on his cock and prostate too much to handle for any longer. Dean slowly pulled his finger out of Castiel’s hole, and Castiel pushed off of Dean’s lap, kneeling on the floor of the backseat. He lapped his own cum off of Dean’s stomach before looking up at Dean.

“You clean?”

“Yeah, Cas. Never been with anyone else. You?”

“Same,” Castiel replied, taking Dean into his mouth without any warning.

Dean moaned, lacing fingers in Castiel’s hair. He'd never had a blow job before, and it was quickly becoming his favorite thing to do. Absently, he wondered whether he'd be able to do as good a job as Castiel was doing, and what Castiel's cock tasted like. “Oh god, Cas. Oh yeah, fuck yeah.”

Castiel wasn’t experienced—he’d never done this before, nor had it done to him—but he knew the basics from watching porn. He bobbed his head, using his hand on Dean’s shaft to cover the parts of Dean’s cock he couldn’t reach. Tonguing the slit on Dean’s cockhead, Castiel looked up at the other boy.

Seeing Castiel’s blue eyes in the moonlight, Dean moaned. “I’m about to cum.”

Castiel just hummed around Dean’s cock, giving him permission to cum in his mouth.

“Fuck,” Dean said, pumping his cum down Castiel’s throat. Castiel kept stroking Dean through his orgasm, swallowing everything and then gently licking Dean's cock clean.

Dean pulled Castiel from the car floor and returned him to his lap, careful to keep their sensitive cocks from rubbing too hard against each other. Dean brought their mouths together, tasting his own salty cum on Castiel’s tongue.

“You’re incredible,” Castiel whispered into Dean’s neck, giving him a small kiss on his Adam’s apple.

“You’re beautiful,” Dean replied. “Would you be my boyfriend?”

“Of course.” Castiel laughed. “I can’t believe a few hours ago you thought I was a girl, and now you want me to be your boyfriend.”

“I would’ve still asked you out had I known earlier. I really like you, Cas.”

“And I really like you.” Nervously, Castiel knew he had to ask one question. “The dresses, the makeup… it doesn’t bother you, does it?”

“Fuck, Cas, I love it. You’re gorgeous. And I definitely have a thing for lace panties. I, um, I hope you don’t mind that I wear them sometimes too?”

“Dean, I would love to see you in panties.”

“Well, that’s settled. Thanks, that’s not something I’ve ever told anyone before. I trust you, so much. This is probably the best date I’ve ever been on.” It was the only date Dean had ever been on.

“Same,” Castiel said, smiling at Dean. It was also the only date Castiel had ever been on.

* * *

“Thus from my lips, by yours, my sin is purged.” Dean moved to kiss Castiel, as they had practiced so many times before, both in rehearsal and outside of it.

“Then have my lips the sin that they have took,” Castiel replied, sweating faintly under the hot stage lights.

Dean was not nervous about the crowd. He was lost in Castiel’s eyes. “Sin from thy lips? O trespass sweetly urged! Give me my sin again.”

“You kiss by the book.” Castiel returned Dean’s kiss, and winked. Their kisses offstage were definitely not ‘by the book,’ but the audience didn't need to know that.


End file.
